In this episode of Dating In Your 20s, Amelia sits down with Lilly to unpack the lessons, heartbreaks, and reality checks that shape so many of our dating experiences in our twenties. Inspired by Dolly Alderton’s book Everything I Know About Love, the conversation explores how dating, friendships, and self-discovery are deeply intertwined during this decade.

Together, Amelia and Lilly dive into the fears and insecurities that surface while navigating relationships, situationships, and the pressure to have it all figured out. They also reflect on the humbling moments when we realize that sometimes it’s not the world that needs changing — it’s our own patterns, expectations, or healing that deserve attention.

This episode is an honest conversation about growth, accountability, friendship, heartbreak, and learning to love yourself before chasing love from someone else. If you’ve ever wondered why dating feels so complicated in your twenties, or found yourself repeating the same relationship cycles, this episode is for you.

In this episode, they discuss:

• Lessons from Everything I Know About Love and how they show up in modern dating
• The fears and insecurities that follow us through our twenties
• Friendship as a foundation for personal and relational growth
• Recognizing unhealthy dating patterns and taking accountability
• The moment you realize growth starts within
• Letting go of timelines and expectations around love and relationships
• Why self-awareness matters more than finding “the one”

Takeaway

Your twenties are less about finding the perfect partner and more about becoming someone you’re proud to be with — and learning along the way that love shows up in many forms, not just romantic ones.

Join the conversation:

What is something dating in your twenties has taught you about yourself? Share your thoughts and stories with us — we’d love to hear them.

Related Episodes:

• The “Village” We Romanticize vs. the Village We Actually Build
• Is Having a Boyfriend Embarrassing?

Dating In Your 20s Anonymous Corner

Check out the anonymous DIY20s Form. It’s a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

Your 20s are basically one ongoing identity crisis — dating feels confusing, friendships feel different than they used to, and everyone seems to be overwhelmed, healing, or “protecting their peace.” In this episode, Amelia and Lilly talk about one of the most underrated parts of dating in your 20s: the people around you matter just as much as the person you’re dating.

This is a conversation about friendship, emotional labor, reciprocity, and what it actually means to build a village — not just want one. Because the truth is, friendships in your 20s don’t happen by accident. They take intention, vulnerability, and a willingness to show up even on the days you’d rather hide under a blanket.

If dating is about who you’re becoming, then friendship is the support system that gets you there.

Takeaways

• Why friendships feel harder to maintain in your 20s
• The pressure to “protect your peace” and how it impacts connection
• Emotional labor as an investment, not a burden
• Reciprocity vs. scorekeeping
• Why crisis moments don’t build friendship — consistency does
• Losing friends, outgrowing friends, and navigating changing dynamics
• Being a “villager”: how to actually show up for your people
• The small, mundane moments that make friendships feel safe
• Understanding when someone can’t show up (and when it’s a pattern)

Related Episodes:

• Is Having a Boyfriend Embarrassing?
• Looking Back, Moving Forward: How Our Podcast Changed Our Relationships With Oren Matteson

Dating In Your 20s Anonymous Corner

We’d love to hear from you! Check out the anonymous DIY20s Form. It’s a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

In today’s dating culture, where everyone is either soft launching, situationshipping, or pretending they don’t care…it almost feels controversial to say you have a boyfriend. Thanks to a recent Vogue article making its rounds, Amelia and Lilly dive into the very real (and very funny) question:

Is having a boyfriend… embarrassing now?

This episode unpacks the weird social pressure young women feel in their 20s: wanting connection, craving independence, and also low-key worrying that posting your boyfriend will ruin your mysterious internet aura.

The hosts break down the cultural shift they’re seeing everywhere: independence is trending, relationships are treated like an aesthetic choice, and the internet has definitely influenced how we feel about commitment.

The Real Takeaway

This Vogue debate isn’t really about boyfriends — it’s about how much pressure we put on ourselves in our 20s to look a certain way, date a certain way, or be single a certain way. The goal?

Do whatever feels right for your life, not your feed.

Takeaways

• Relationship culture has changed — independence is trendy, and commitment gets weirdly judged.
• Social media shapes how we think our love lives “should” look.
• Whether you’re single, cuffed, or somewhere in-between, your identity doesn’t disappear.
• Being in a relationship isn’t embarrassing — pretending you don’t want connection might be.

Related Episodes:

• Ghosts of Boyfriends Past
• The Crash-out Episode

Dating In Your 20s Anonymous Corner

We’d love to hear from you! Check out the anonymous DIY20s Form. It’s a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

In this episode, Amelia and Lilly dive into the idea of personal growth through relationships—how every connection, whether positive or painful, can become a mirror for self-development. Lilly shares her reflections on learning to recognize and celebrate growth, emphasizing the importance of honoring both the messy and meaningful parts of the journey. Together, they unpack how relationships shape who we become and why self-celebration is an essential, often overlooked, part of healing and growth.

Takeaways

• Even negative experiences can spark growth.
• Positive relationships also teach us valuable lessons.
• Celebrating your own growth is essential to healing.
• Growth isn’t linear—it’s circular, layered, and evolving.
• Recognizing growth moments fosters self-pride and self-awareness.
• Relationships reflect our patterns, progress, and potential.
• Growth means honoring both challenges and achievements.

Related Episodes:

• The Ten Commandments
• Why You Ghost, Cling, or Chase: Attachment Styles with Hilary Rosenberg

Dating In Your 20s Anonymous Corner

We'd love to hear from you! Check out the anonymous DIY20s Form. It's a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

In this episode, Amelia and Lilly recap their time at the Beauty Boost Chicago event and reflect on the power of community and supporting local businesses. They revisit the mission behind their podcast — offering a therapeutic lens on dating and relationships — and dive into the “unwritten rules” of modern dating. Together, they question these societal commandments, encouraging listeners to decenter external expectations and reconnect with their own values.

The conversation touches on navigating feedback from friends and family, the messy process of self-discovery in your 20s, and practicing compassionate curiosity toward yourself and others. Amelia and Lilly close with a reminder that there’s no single “right” way to date — just your way — and invite listeners to embrace their unique experiences and seek support along the journey.

Takeaways

• The Beauty Boost Chicago event showcased local businesses and communities.
• Listeners appreciate the therapeutic approach to dating discussed in the podcast.
• Societal rules around dating can create unnecessary pressure.
• It's important to focus on personal values rather than external expectations.
• Feedback from friends and family can complicate dating decisions.
• Self-discovery is a crucial part of navigating relationships in your 20s.
• Embracing change is essential for personal growth.
• Compassionate curiosity helps in understanding oneself better.
• It's okay to feel uncomfortable when spending time alone.
• The journey of dating is unique for everyone, and there's no one-size-fits-all approach.

Related Episodes:

• The Crash-out Episode
• Looking Back, Moving Forward: How Our Podcast Changed Our Relationships With Oren Matteson

Dating In Your 20s Anonymous Corner

We'd love to hear from you! Check out the anonymous DIY20s Form. It's a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

In this episode of 'Dating in Your 20s', therapists Lilly Wehman and Amelia Abernathy share their personal experiences and insights on the emotional challenges of dating in their twenties. They discuss the vulnerability of early dating stages, the extremes of emotional responses, and the importance of community and shared experiences. The conversation emphasizes the need for coping mechanisms and small steps to regain control amidst the chaos of dating, while also promoting an upcoming community event for listeners.

Takeaways

• Clients are experiencing heightened anxiety over dating responses.
• Vulnerability is a common theme in early dating stages.
• Jumping to conclusions can lead to unnecessary anxiety.
• Communication is key to avoiding ghosting.
• Finding balance between extremes is essential for emotional health.
• The middle ground in dating can be a safe space.
• Coping mechanisms can be small but effective.
• Community support is vital during dating struggles.
• It's okay to seek help and share experiences with others.

Link to the event we’ll be at: https://www.thebeautyboost.net/events/sip-social-spook

Related Episodes:

• Looking Back, Moving Forward: How Our Podcast Changed Our Relationships With Oren Matteson
• Putting Yourself Out There (Ugh) The brave act of dating with anxiety

Dating In Your 20s Anonymous Corner

We'd love to hear from you! Check out the anonymous DIY20s Form. It's a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

In this episode, Oren Matteson sits down with Dating in Your 20s hosts Amelia Abernathy and Lilly Wehman to reflect on their podcast journey so far. Together, they explore how their conversations about dating, growth, and self-awareness have shaped their own relationships and perspectives. The trio dives into topics like communication, setting intentions, evolving expectations in modern dating, and what commitment really looks like in your twenties. They also share what’s next for the podcast and how it continues to evolve alongside their personal lives.

Takeaways

• The podcast started as a resource for clients.
• Lilly and Amelia's relationship has deepened through their discussions.
• The podcast has helped them connect with friends and clients.
• Amelia feels less different in her dating experiences.
• Conversations on the podcast have made them more confident.
• Dating is seen as fun and exciting, not embarrassing.
• Expectations in dating are influenced by media and societal norms.
• Communication is key to understanding intentions in dating.
• Commitment is a signal to begin the hard work in relationships.
• They aspire to create more interactive content for their audience.

Related Episodes:

• The Narcissism Conversation: What’s Real, What’s Overused, and How to Heal With DeVona Alleyne
• Dating in Your 20s Series: Male Perspectives on Dating with Oren Matteson

Dating In Your 20s Anonymous Corner

We'd love to hear from you! Check out the anonymous DIY20s Form. It's a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn
Oren Matteson: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

In this episode of Dating in Your 20s, Amelia and Lilly sit down with Rev. DeVona Alleyne, LCPC, Clinical Director at Millennium Counseling Center, for a candid conversation about the complexities of narcissism in relationships.

Together, they break down:

• The traits of narcissistic tendencies and how they can show up in dating
• The phenomenon of love bombing and its emotional aftermath
• The role of gaslighting and why it can be so disorienting
• How to recognize red flags and set boundaries
• The importance of self-awareness and compassion—for both yourself and others

DeVona shares wisdom from her clinical perspective and pastoral lens, offering guidance on how to protect your mental and emotional health while navigating the highs and lows of dating in your 20s.

This episode is an honest and empowering look at how to prioritize your needs, trust your instincts, and approach relationships with clarity and confidence.

Takeaways

Narcissistic tendencies can manifest as a lack of empathy.
Love bombing often covers up underlying shame.
Recognizing red flags early can prevent emotional turmoil.
Gaslighting is a common tactic used by narcissists.
Setting boundaries is crucial in any relationship.
Compassion for those with narcissistic tendencies is important.
Attachment styles can influence relationship dynamics.
Dating in your 20s requires self-awareness and reflection.
It's essential to prioritize your own needs in relationships.
Healthy relationships should allow for personal boundaries.

Related Episodes:

• The DMs Are Open: Listener Q&A
• Why You Ghost, Cling, or Chase: Attachment Styles with Hilary Rosenberg

Dating In Your 20s Anonymous Corner

We'd love to hear from you! Check out the anonymous DIY20s Form. It's a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn
Rev. DeVona Alleyne: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

In this episode of Dating in Your 20s, Amelia and Lilly answer questions straight from you — our listeners. Think of it as your very own dating hotline, where we dive into the real challenges, worries, and curiosities that come with navigating relationships in your 20s.

From ghosting and mixed signals to boundaries and confidence, nothing is off the table. These are the questions you’ve been DMing us, and we’re unpacking them with honesty, humor, and a therapist’s perspective.

✨ What you’ll hear in this episode:

• Real talk about the biggest challenges women face in dating today
• How modern dating culture impacts expectations and emotions
• The balance between knowing your worth and staying open to love
• Practical tools for confidence, boundaries, and clarity in relationships

Related Episodes:

• Ghosts of Boyfriends Past
• What to Do When You’re the Last Single One

Dating In Your 20s Anonymous Corner

We'd love to hear from you! Check out the anonymous DIY20s Form. It's a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | Linkedin

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

The Ghosts of Boyfriends Past — we all have them, but how much do they actually shape who we are in relationships today? In this episode of Dating in Your 20s, Amelia and Lilly spill the tea on how exes linger in our minds and what it means for dating in the here and now. From the emotional baggage that sneaks into new relationships to the little patterns we repeat without realizing it, we’re unpacking it all.

We’ll talk about things like projection (a.k.a. putting your old partner’s stuff on your new one), transference (when your new boo gets blamed for what your ex did), and hypervigilance (the overthinking spiral where you’re constantly on guard). Sounds heavy, but don’t worry—we’re mixing the real talk with laughter, honesty, and a little bit of therapy wisdom.

Therapeutic Takeaways

• Awareness is everything. The first step in breaking old patterns is noticing when your ex’s “ghost” shows up in your current relationship.
• Give yourself grace. Healing isn’t linear—past relationships leave marks, but they don’t have to define your future.
• Stay curious, not critical. Instead of judging yourself for slipping into old habits, ask: “What is this trying to teach me?”
• Therapy helps. Talking about your “ghosts” in a safe space can help you release what’s no longer serving you.

Whether you’re haunted by an old situationship or just want to better understand your dating brain, this episode is your permission slip to face the ghosts, laugh at the cringe, and grow in the process.

Related Episodes:

• Is 'The One' Even Real? Unpacking Soulmate Myths and Dating with Intention
• Breadcrumbing, Benching, and Other Bullsh*t: Modern dating behaviors that mess with your head

Dating In Your 20s Anonymous Corner

We'd love to hear from you! Check out the anonymous DIY20s Form. It's a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | Linkedin

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com